(4E,5R)-4-[2-[(1R,4aR,5R,6R,8aS)-6-hydroxy-5,8a-dimethyl-2-methylidene-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-5-hydroxyoxolan-3-one

Details

• Internal ID: f6629623-1bb1-4efe-91a8-6d363774f5ab
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > O-glycosyl compounds
• IUPAC Name: (4E,5R)-4-[2-[(1R,4aR,5R,6R,8aS)-6-hydroxy-5,8a-dimethyl-2-methylidene-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-5-hydroxyoxolan-3-one
• SMILES (Canonical): CC12CCC(C(C1CCC(=C)C2CC=C3C(OCC3=O)O)(C)COC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): C[C@@]12CC[C@H]([C@@]([C@@H]1CCC(=C)[C@H]2C/C=C/3\[C@@H](OCC3=O)O)(C)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C26H40O10/c1-13-4-7-18-25(2,15(13)6-5-14-16(28)11-34-23(14)33)9-8-19(29)26(18,3)12-35-24-22(32)21(31)20(30)17(10-27)36-24/h5,15,17-24,27,29-33H,1,4,6-12H2,2-3H3/b14-5-/t15-,17-,18-,19-,20-,21+,22-,23-,24-,25+,26+/m1/s1
• InChI Key: FAONOYVYMFUUOU-IAXFXGECSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₀O₁₀
• Molecular Weight: 512.60 g/mol
• Exact Mass: 512.26214747 g/mol
• Topological Polar Surface Area (TPSA): 166.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.21
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7469	74.69%
Caco-2	-	0.8240	82.40%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7735	77.35%
OATP2B1 inhibitior	-	0.5812	58.12%
OATP1B1 inhibitior	+	0.8728	87.28%
OATP1B3 inhibitior	+	0.9273	92.73%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.5221	52.21%
P-glycoprotein substrate	-	0.7334	73.34%
CYP3A4 substrate	+	0.7242	72.42%
CYP2C9 substrate	-	0.8007	80.07%
CYP2D6 substrate	-	0.8783	87.83%
CYP3A4 inhibition	-	0.9013	90.13%
CYP2C9 inhibition	-	0.9158	91.58%
CYP2C19 inhibition	-	0.9084	90.84%
CYP2D6 inhibition	-	0.9256	92.56%
CYP1A2 inhibition	-	0.8918	89.18%
CYP2C8 inhibition	+	0.4781	47.81%
CYP inhibitory promiscuity	-	0.9396	93.96%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6268	62.68%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9375	93.75%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7134	71.34%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.7198	71.98%
skin sensitisation	-	0.9025	90.25%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.6458	64.58%
Acute Oral Toxicity (c)	I	0.6455	64.55%
Estrogen receptor binding	+	0.7236	72.36%
Androgen receptor binding	+	0.6810	68.10%
Thyroid receptor binding	-	0.4944	49.44%
Glucocorticoid receptor binding	+	0.5974	59.74%
Aromatase binding	+	0.7114	71.14%
PPAR gamma	+	0.6452	64.52%
Honey bee toxicity	-	0.6662	66.62%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9678	96.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.46%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	93.42%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.51%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.70%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.03%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.04%	95.56%
CHEMBL237	P41145	Kappa opioid receptor	87.23%	98.10%
CHEMBL1937	Q92769	Histone deacetylase 2	86.19%	94.75%
CHEMBL226	P30542	Adenosine A1 receptor	86.02%	95.93%
CHEMBL1977	P11473	Vitamin D receptor	85.19%	99.43%
CHEMBL2581	P07339	Cathepsin D	85.01%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.76%	96.61%
CHEMBL5028	O14672	ADAM10	83.70%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.23%	89.00%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.01%	90.24%
CHEMBL5255	O00206	Toll-like receptor 4	80.28%	92.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.07%	94.33%

Plants that contains it

• Andrographis paniculata

Cross-Links

• PubChem: 163045492
• LOTUS: LTS0158689
• wikiData: Q104992371